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2,5-ジ-tert-アミルヒドロキノン

2,5-Di-t-pentylhydroquinone

HCID 6610
ノート反応
基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
79-74-3
標準SMILES
CCC(C)(C)c1cc(O)c(C(C)(C)CC)cc1O
InChIKey
CZNRFEXEPBITDS-UHFFFAOYSA-N
分子式
C16H26O2
平均分子量
250.38 g/mol
単同位体質量
250.19328007

名称と識別子

優先名称
2,5-Di-t-pentylhydroquinone
IUPAC
2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol
現地名
2,5-ジ-tert-アミルヒドロキノン
英語名
2,5-Di(tert-amyl)hydroquinone
分子式
C16H26O2
分子量
250.38

名称と別名

79-74-32,5-Di-tert-amylhydroquinone2,5-Di-tert-pentylbenzene-1,4-diol2,5-Di-tert-pentylhydroquinoneSantovar ADiamylhydroquinoneAntage DAHUSAF B-211,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-2,5-DI(TERT-AMYL)HYDROQUINONE2,5-Di-t-amylhydroquinone2,5-Bis(1,1-dimethylpropyl)hydroquinone
名称をさらに表示
2,5-ジ-tert-アミルヒドロキノン2,5-ジ-tert-ペンチルヒドロキノン2,5-ビス(1,1-ジメチルプロピル)ベンゼン-1,4-ジオール2,5-ビス(tert-ペンチル)ヒドロキノンサントバルA2,5-ジ-tert-ペンチルベンゼン-1,4-ジオール2,5-ビス(1,1-ジメチルプロピル)ヒドロキノンサントバールA2,5ジtアミルヒドロキノン2,5-ジ-tert-アミルハイドロキノン2,5-ジ-T-ペンチルヒドロキノンDAHkyhjdahqSantovarusafb-21santouarasantovaraantagedahSantouar A
Hydroquinone, 2,5-di-tert-pentyl-Hydroquinone, 2,5-di-t-pentyl-NSC 455Hydroquinone, 2,5-di-tert-amyl-2,5-DI-T-PENTYLHYDROQUINONE2,5-Di-tert-amylbenzene-1,4-diol2,5-Bis(1,1-dimethylpropyl)-1,4-benzenediolHSDB 5231

データベース識別子

CAS
79-74-3
PubChem CID
6610
DTXSID
DTXSID5044992
ChEMBL
CHEMBL594135
UNII
19O4J76TTK
EC Number
201-222-2
Nikkaji
J10.508B

物性

構造計算による物性

XLogP
5.6
極性表面積
40.5 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
4
重原子数
18
形式電荷
0
複雑度
242

実験および物理化学的性質

Chemical ClassesOther Classes -> Phenols
CosmeticsAntioxidant
Density1.05 @ 25 °C
Color/Form · 2 件

CRYSTALS

BUFF POWDER

SolubilitySLIGHTLY SOL IN WATER; SOL IN ALCOHOL & BENZENE
Melting Point179.4-180.4 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 2 件

Dry Powder

Beige solid; [HSDB]

物理化学的性質

融点
179 °C · 179 °C
沸点
353.51 °C · 353.51°C (rough estimate)
比重(密度)
0.9781 · 0.9781 (rough estimate)
蒸気圧
0 Pa · 0Pa at 20℃
屈折率
1.6 · 1.6000 (estimate)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

危険有害性情報

Regulatory Information · 4 件

Chemical: 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 2,5-di-tert-pentylhydroquinone (EC: 201-222-2)

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Reproductive effector; Causes liver injury (abnormal liver function tests) and weight loss in feeding studies; [RTECS] Emergency treatment: see Hydroquinone and Quinone. [HSDB] An irritant; May cause skin burns and damage to lungs; [MSDSonline]

Hazard Classes and Categories · 3 件

Acute Tox. 4 (100%)

Specific target organ toxicity - Single exposure - Category 2 (systemic toxicity)

Skin sensitization - Category 1A

安全と保護具

Disposal Methods

化学と産業

薬理情報

Absorption, Distribution and ExcretionCMPD WAS FOUND IN TISSUES INCL NEUROLOGICAL TUMORS, ADULT & FETAL BRAIN. NO CONTAMINATION SOURCE WAS FOUND IN HOSPITAL; POSSIBLE SOURCE: ANTIOXIDANT PREPN IN RUBBER MFR.

用途と製造

Uses · 3 件

Used as an antioxidant for uncured rubber and unsaturated resins and oils; in food packaging; as a polymerization inhibitor; and as a staining protector in rubber; [HSDB]

ANTIOXIDANT FOR UNCURED RUBBER & FOR UNSATURATED RESINS & OILS; FOOD PACKAGING; POLYMERIZATION INHIBITOR

AS STAINING PROTECTOR IN RUBBER

U.S. Production2023: <50,000 lb
Industry UsesAntioxidant
Methods of Manufacturing · 2 件

ERICKSON, BRITISH PATENT 596,461 (1948 TO MATHIESON ALKALI WORKS).

Hydroquinone + isoamylene (Friedel-Crafts alkylation)

Use ClassificationCosmetics -> Antioxidant
General Manufacturing Information · 2 件

Plastics Material and Resin Manufacturing

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-: ACTIVE

応用分野

用途ゴムの防汚剤、未硬化ゴム?不飽和樹脂?油の酸化防止剤、食品包装、重合禁止剤

用途有機合成原料。

調製方法

純化方法Crystallise the hydroquinone under N2 from boiling AcOH (7mL/g) plus boiling water (2.5mL/g). [Stolow & Bonaventura J Am Chem Soc 85 3636 1963]. Store it in sealed ampoules under N2 away from light. [Beilstein 6 H 952, 6 III 4748.]

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
酸解離定数(Pka)
11.21 · 11.21±0.23(Predicted)
外見
powder to crystal
色
White to Yellow to Orange
水溶解度
200 ng/L · 200ng/L at 20℃
Merck
14 · 14,3304
化粧品成分の機能
抗酸化物質
LogP
5.1 at · 5.1 at 25℃
CAS データベース
79 · 79-74-3(CAS DataBase Reference)
NISTの化学物質情報
1 · 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-(79-74-3)
EPAの化学物質情報
1 · 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- (79-74-3)
· 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

毒性情報

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
TSCA Test Submissions · 5 件

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for dermal sensitization. The Shelanski and Shelanski Repeated Insult Patch Test was used, the test substance was administered to more than 50 adults. The induction phase included 10 occluded applications of 0.2 ml of a 50% dispersion of test substance to the intact skin on the left side of the back. No adverse responses occurred in 21 subjects. In another 21 subjects, responses not greater than a Grade 1 occurred. In 5 subjects, responses not greater than a Grade 2 occurred. Indurated erythematous (Grade 4) occurred once in 6 subjects and twice in 1 subject. Five weeks after the induction phase, the challenge phase included application of the test substance to naive sites at the same concentration as the induction phase. No adverse responses occurred in 37 subjects. In 9 subjects, responses not greater than a Grade 1 occurred. In 4 subjects, responses not greater than a Grade 2 occurred. In 3 subjects, a Grade 4 was obtained after the second application of the challenge phase. The test substance was determined to have a weak to moderate skin-irritating propensity.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for teratogenic toxicity. The test substance was administered orally in a corn oil vehicle to pregnant Sprague-Dawley rats (25/group) at dosage levels of 0, 20, 70, or 175 mg/kg/day on gestation days 6-15. All doses were administered at a constant volume of 5 mg/kg. Clinical signs at 70 mg/kg/day were slight maternal toxicity and substantial maternal toxicity at 175 mg/kg/day. Signs of toxicity included post-dosing salivation, increased incidence of reddish colored vaginal discharge at the 70 mg/kg/day level, and more frequent and severe toxicity, body weight loss and reduced food consumption at the 175 mg/kg/day level. Fetal toxicity at 175 mg/kg/day, included statistically significant body weight loss and litters with ossification variations, such as an increased incidence of skull anomalies, 7th cervical ribs, and #5 and/or #6 sternebrae were unossified. The no observable effect level (NOEL) for maternal toxicity was 20 mg/kg/day, and the NOEL for developmental toxicity was 70 mg/kg/day.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for the potential to induce structural chromosomal aberrations in the hemopoietic cells of the rat bone marrow when administered by oral gavage. The test substance was administered in single oral doses to three groups of fasted young albino Sprague-Dawley rats (number and sex of rats was not reported) at a dosage of 1000 mg/kg of body weight. Treated rats were evaluated at intervals of 6, 18, and 30 hours. Approximately 2 hours before each sacrifice time, rats were administered colchicine at 4 mg/kg of body weight to arrest cells in metaphase. Both femurs were removed from sacrificed animals and metaphase slides were prepared for scoring of chromosome aberrations. All rats exhibited mild to severe toxic signs, including diarrhea, abnormal gait, and stance. In the 18 hour group, toxic signs included decreased body tone and inactivity. In the 30 hour group, toxic signs included yellow to brown wet pellage in the anal-genital region and decreased body tone. From the 18 hour harvest group 2 females died. From each animal, 50 metaphase cells were analyzed. There were no statistically significant increase in the incidence of aberrations or number of aberrant metaphases observed at any of the three sampling times, therefore, the test substance was classified as not clastogenic.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for mutagenicity in the rat liver homogenate metabolic activation system (S9). The test substance was tested in an insoluble concentration in aqueous media (greater than 100 ug/ml). Increases in cytotoxicity were observed as the S9 levels increased from 2% to 10%. Maximum concentrations tested in mutagenicity assays were 150 ug/ml in the absence of S9 and 100 ug/ml in the presence of 1%, 2%, 5%, and 10% S9. The test substance was determined not to be a mutagen.

For more TSCA Test Submissions (Complete) data for 2,5-DI-T-PENTYLHYDROQUINONE (6 total), please visit the HSDB record page.

Human Toxicity ExcerptsChronic neurotoxic effects include vision disturbances. /From table; Quinones/
Non-Human Toxicity Excerpts · 4 件

2,5-DITERTIARY AMYL HYDROQUINONE WAS NON-HEMOLYTIC IN NORMAL RAT ERYTHROCYTES.

AFTER POS MATING OF WALTER REED-CARWORTH FARMS RATS IN THEIR 1ST GESTATION, FEMALES WERE RANDOMLY DISTRIBUTED INTO EXPTL & CONTROL GROUPS, FORMER GIVEN 2,5-DI-TERT-AMYLHYDROQUINONE BY MOUTH OR INTO DIET & KILLED 21 DAYS AFTER MATING. DATA SUGGEST BENEFICIAL EFFECT ON RESORPTION RATE.

Acute neurotoxic effects reported in animals include convulsions; medullary paralysis. /From table; Quinones/

The effects of diethyl maleate on the cytotoxicity of phenyl-hydroquinone and other hydroquinones were studied in freshly isolated rat hepatocytes. Addition of phenyl hydroquinone (O.5 or 0.75 mM) to hepatocytes resulted in dose-dependent cell death accompanied by the abrupt depletion of both glutathione and protein thiols and the accumulation of phenyl-benzoquinone. Pretreatment with diethyl maleate (1.25 mM) which causes an abrupt depletion of cellular glutathione in hepatocytes delayed the onset of phenyl hydroquinone-induced cytotoxicity. The delay correlated with inhibition of phenyl benzoquinone formation. Among other hydroquinones (0.5 mM), tert-butyl-hydroquinone-induced cytotoxicity was decreased by diethyl maleate (1.25 mM), but diethyl maleate did not affect the cytotoxicity of 2,5-di(tert-butyl)-1,4-benzohydroquinone. Phenyl-hydroquinone -induced cytotoxicity correlated with the accumulation of phenyl-benzoquinone in the cell.

安全データ

wgk
3
tsca
TSCA listed
rtecs
MX6300000
hs_code
2914.69.9000
化審法
(3)-553
有毒物質データの
79-74-3(Hazardous Substances Data)

上流・下流製品情報

上流原料

2,5-ジ-tert-アミルベンゾキノン硫酸水素2-メチル-2-ブテンヒドロキノン

下流製品

2-エトキシフェノール3,5-ジ-tert-ブチルカテコール

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